Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 36, Pages 8182-8190Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403111
Keywords
Diastereoselectivity; Cycloaddition; Oxidation; Microwave chemistry; Phenanthridines
Categories
Funding
- Norwegian Research Council [209330]
- Bruker Avance
- ERASMUS program
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Phenanthridines functionalized in the C-ring have been synthesized by IMDAF (intramolecular Diels-Alder reaction on furans) cyclization of ortho-furyl(alkenylamino)arenes under both microwave and conventional heating conditions. The outcomes of the reactions are highly dependent on the substitution patterns both on the dienophile and on the arene components. 5,6-Dihydrophenanthridines, which can easily be oxidized to fully aromatic phenanthridines, are formed under microwave conditions as long as the Diels-Alder adduct contains a hydrogen atom in the 6a-position. Aromatization of the phenanthridine C-ring does not occur when the cyclization is performed under conventional heating conditions. The IMDAF reaction can, under these conditions, lead to Diels-Alder adducts or to phenanthridines with partially saturated and functionalized C-rings, depending on the detailed structure of the starting material.
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